2-trimethylsilylethyl (2Z,6E,8Z,10S,13R)-15-hydroxy-17-[(4R)-3-(methoxymethyl)-2-oxo-1,3-thiazolidin-4-yl]-3,10-dimethyl-17-oxo-13-(2-trimethylsilylethoxymethoxy)heptadeca-2,6,8-trienoate | 1027024-33-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-trimethylsilylethyl (2Z,6E,8Z,10S,13R)-15-hydroxy-17-[(4R)-3-(methoxymethyl)-2-oxo-1,3-thiazolidin-4-yl]-3,10-dimethyl-17-oxo-13-(2-trimethylsilylethoxymethoxy)heptadeca-2,6,8-trienoate
• CAS: 1027024-33-4
• 化学式: C₃₅H₆₃NO₈SSi₂
• 分子量: 714.124
• InChiKey: SYHHPPARBSTXAX-VKMQUYEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  47
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-trimethylsilylethyl (2Z,6E,8Z,10S,13R)-15-hydroxy-17-[(4R)-3-(methoxymethyl)-2-oxo-1,3-thiazolidin-4-yl]-3,10-dimethyl-17-oxo-13-(2-trimethylsilylethoxymethoxy)heptadeca-2,6,8-trienoate 在 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二甲基亚砜 为溶剂， 生成 (1R,4Z,7a'S,8E,10Z,12S,15R,17S)-5,12-dimethyl-7',7a'-dihydro-3'H,5'H-2,16-dioxaspiro[bicyclo[13.3.1]nonadecane-17,1'-thiazolo[3,4-c]oxazole]-4,8,10-triene-3,5'-dione
  参考文献：
  名称：

  Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer

  摘要：

  Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, beta-keto ester 27, and phosphonium salt 26, which established the conjugated EZ-diene moiety of 31. The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection. Final lactonization of 47 was carried out using the Mitsunobu protocol. A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.

  DOI：

  10.1021/jo00046a008
• 作为产物：
  描述：

  (2E,6E,8Z)-(10S,13R)-15-(tert-Butyl-dimethyl-silanyloxy)-3-(diethoxy-phosphoryloxy)-10-methyl-13-(2-trimethylsilanyl-ethoxymethoxy)-pentadeca-2,6,8-trienoic acid 2-trimethylsilanyl-ethyl ester 在 cerium(III) chloride 、 草酰氯 、 pyridinyl p-toluenesulfonate 、 methylcopper 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 3.67h， 生成 2-trimethylsilylethyl (2Z,6E,8Z,10S,13R)-15-hydroxy-17-[(4R)-3-(methoxymethyl)-2-oxo-1,3-thiazolidin-4-yl]-3,10-dimethyl-17-oxo-13-(2-trimethylsilylethoxymethoxy)heptadeca-2,6,8-trienoate
  参考文献：
  名称：

  Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer

  摘要：

  Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, beta-keto ester 27, and phosphonium salt 26, which established the conjugated EZ-diene moiety of 31. The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection. Final lactonization of 47 was carried out using the Mitsunobu protocol. A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.

  DOI：

  10.1021/jo00046a008

文献信息

• Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer
  作者：James D. White、Motoji Kawasaki

  DOI：10.1021/jo00046a008

  日期：1992.9

  Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, beta-keto ester 27, and phosphonium salt 26, which established the conjugated EZ-diene moiety of 31. The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection. Final lactonization of 47 was carried out using the Mitsunobu protocol. A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.